Methyl iodide → methyl 3-bromo-5-fluoro-2-methylbenzoate

HRID 1809468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809468
[C:1]([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([OH:13])=[O:12].IC>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([O:13][CH3:1])=[O:12]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666439353-bromo-5-fluoro-2-methylbenzoic acid

Produkt 1

HCID 68633230methyl 3-bromo-5-fluoro-2-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

K2CO3 (1.2 eq.) was added to a solution of (E3) in DMF (0.26 M) and the resulting suspension was stirred at RT for 30 min. Then, iodomethane (1.2 eq.) was added and the reaction mixture was stirred at RT overnight. The solution was diluted in EtOAc and the organic phase was washed with brine and dried (Na2SO4). Solvent was removed in vacuo giving a residue that was purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49) yielding (31% over 4 steps) the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 7.74 (1H, dd, J=8.4 and 2.8 Hz), 7.60 (1H, dd, J=7.3 and 2.5 Hz), 3.95 (3H, s), 2.59 (3H, s).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at RT overnight
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed in vacuo
  5. customgiving a residue that
  6. customwas purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49)

Quellen und Nachweise

ORD-Eintrag
ord-df9a953acf33455baf3f7683c448a36a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362030B2

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